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MedKoo Cat#: 100973 | Name: Eribulin mesylate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eribulin is a synthetic analog of halichondrin B and acts as a microtubule dynamics inhibitor with potent antineoplastic activity. Its primary mechanism is irreversible binding to the plus ends of microtubules, thereby suppressing microtubule polymerization without affecting depolymerization, leading to G2/M cell cycle arrest and apoptosis. In vitro, eribulin exhibits nanomolar potency against a wide range of cancer cell lines, with IC₅₀ values typically ranging from 0.1 to 10 nM (e.g., IC₅₀ = 0.3 nM in MDA-MB-231 breast cancer cells). In vivo, eribulin shows significant tumor growth inhibition in xenograft models of breast, lung, and prostate cancers.

Chemical Structure

Eribulin mesylate
Eribulin mesylate
CAS#441045-17-6 (mesylate)

Theoretical Analysis

MedKoo Cat#: 100973

Name: Eribulin mesylate

CAS#: 441045-17-6 (mesylate)

Chemical Formula: C41H63NO14S

Exact Mass: 0.0000

Molecular Weight: 826.01

Elemental Analysis: C, 59.62; H, 7.69; N, 1.70; O, 27.12; S, 3.88

Price and Availability

Size Price Availability Quantity
1mg USD 750.00 2 Weeks
2mg USD 1,250.00 2 Weeks
5mg USD 2,950.00 2 Weeks
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Related CAS #
253128-41-5 (free base) 441045-17-6 (mesylate)
Synonym
Eribulin Mesylate; Eribulin mesilate; Eribulin (mesylate); E7389; E-7389; E 7389; ER-086526; ER 086526; ER086526;
IUPAC/Chemical Name
11,15:18,21:24,28-Triepoxy-7,9-ethano-12,15-methano-9H,15H-furo(3,2-i)furo(2',3':5,6)pyrano(4,3-b)(1,4)dioxacyclopentacosin-5(4H)-one, 2-((2S)-3- amino-2-hydroxypropyl)hexacosahydro-3-methoxy-26-methyl-20,27-bis(methylene)-, 2R,3R,3aS,7R,8aS,9S,10aR,11S,12R,13aR,13bS,15S,18S,21S,24S,26R,28R,29aS)-, methanesulfonate
InChi Key
QAMYWGZHLCQOOJ-WRNBYXCMSA-N
InChi Code
InChI=1S/C40H59NO11.CH4O3S/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41;1-5(2,3)4/h19,23-39,43H,2-3,5-18,41H2,1,4H3;1H3,(H,2,3,4)/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+;/m1./s1
SMILES Code
CO[C@H]1[C@@H](C[C@H](O)CN)O[C@H]2C[C@H]3O[C@@H](CC[C@@H]4O[C@@H](CC[C@@]56C[C@H]7O[C@@H]8[C@@H](O[C@H]9CC[C@H](CC(=O)C[C@H]12)O[C@@H]9[C@@H]8O5)[C@H]7O6)CC4=C)C[C@@H](C)C3=C.CS(=O)(=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
The mesylate salt was approved by the U.S. Food and Drug Administration on November 15, 2010.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Eribulin mesylate (E7389 mesylate) is a microtubule targeting agent that is used for the research of metastatic breast cancer.
In vitro activity:
Eribulin dose-dependently reduced viable cell numbers of all four lines (Fig. 1A), with the highest potency against the Hewga-CCS line (IC50 = 0.69 nmol/L), followed by KAS (1.91 nmol/L), MP-CCS-SY (2.21 nmol/L), and SU-CCS1 (2.21 nmol/L). Reference: Mol Cancer Ther. 2020 Mar;19(3):742-754. https://pubmed.ncbi.nlm.nih.gov/31796507/
In vivo activity:
Eribulin exhibits potent antitumor activity against synovial sarcoma in a tumor xenograft model and that tumor vessels frequently have intervascular pillars, a hallmark of intussusceptive angiogenesis (IA), after the administration of eribulin. Reference: Biochem Biophys Res Commun. 2021 Jul 15;570:89-95. https://pubmed.ncbi.nlm.nih.gov/34274851/
Solvent mg/mL mM
Solubility
DMSO 100.0 121.06
Ethanol 100.0 121.06
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 826.01 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Nakai S, Tamiya H, Imura Y, Nakai T, Yasuda N, Wakamatsu T, Tanaka T, Outani H, Takenaka S, Hamada K, Myoui A, Araki N, Ueda T, Yoshikawa H, Naka N. Eribulin Suppresses Clear Cell Sarcoma Growth by Inhibiting Cell Proliferation and Inducing Melanocytic Differentiation Both Directly and Via Vascular Remodeling. Mol Cancer Ther. 2020 Mar;19(3):742-754. doi: 10.1158/1535-7163.MCT-19-0358. Epub 2019 Dec 3. PMID: 31796507. 2. Watanabe K, Yui Y, Sasagawa S, Suzuki K, Kanamori M, Yasuda T, Kimura T. Low-dose eribulin reduces lung metastasis of osteosarcoma in vitro and in vivo. Oncotarget. 2019 Jan 4;10(2):161-174. doi: 10.18632/oncotarget.26536. PMID: 30719211; PMCID: PMC6349434. 3. Taguchi E, Horiuchi K, Senoo A, Susa M, Inoue M, Ishizaka T, Rikitake H, Matsuhashi Y, Chiba K. Eribulin induces tumor vascular remodeling through intussusceptive angiogenesis in a sarcoma xenograft model. Biochem Biophys Res Commun. 2021 Jul 15;570:89-95. doi: 10.1016/j.bbrc.2021.07.033. Epub ahead of print. PMID: 34274851. 4. Wu NF, Yamamoto J, Aoki Y, Bouvet M, Hoffman RM. Eribulin Inhibits Osteosarcoma in a Clinically-accurate Bone-tumor-insertion PDOX Mouse Model. Anticancer Res. 2021 Apr;41(4):1779-1784. doi: 10.21873/anticanres.14943. PMID: 33813382.
In vitro protocol:
1. Nakai S, Tamiya H, Imura Y, Nakai T, Yasuda N, Wakamatsu T, Tanaka T, Outani H, Takenaka S, Hamada K, Myoui A, Araki N, Ueda T, Yoshikawa H, Naka N. Eribulin Suppresses Clear Cell Sarcoma Growth by Inhibiting Cell Proliferation and Inducing Melanocytic Differentiation Both Directly and Via Vascular Remodeling. Mol Cancer Ther. 2020 Mar;19(3):742-754. doi: 10.1158/1535-7163.MCT-19-0358. Epub 2019 Dec 3. PMID: 31796507. 2. Watanabe K, Yui Y, Sasagawa S, Suzuki K, Kanamori M, Yasuda T, Kimura T. Low-dose eribulin reduces lung metastasis of osteosarcoma in vitro and in vivo. Oncotarget. 2019 Jan 4;10(2):161-174. doi: 10.18632/oncotarget.26536. PMID: 30719211; PMCID: PMC6349434.
In vivo protocol:
1. Taguchi E, Horiuchi K, Senoo A, Susa M, Inoue M, Ishizaka T, Rikitake H, Matsuhashi Y, Chiba K. Eribulin induces tumor vascular remodeling through intussusceptive angiogenesis in a sarcoma xenograft model. Biochem Biophys Res Commun. 2021 Jul 15;570:89-95. doi: 10.1016/j.bbrc.2021.07.033. Epub ahead of print. PMID: 34274851. 2. Wu NF, Yamamoto J, Aoki Y, Bouvet M, Hoffman RM. Eribulin Inhibits Osteosarcoma in a Clinically-accurate Bone-tumor-insertion PDOX Mouse Model. Anticancer Res. 2021 Apr;41(4):1779-1784. doi: 10.21873/anticanres.14943. PMID: 33813382.
1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Eribulin. 2023 Feb 15. PMID: 36780412. 2: Hara Y, Fukumoto S, Mori S, Goto H, Matsumoto K, Enomoto K, Tada K. Prevention of New Metastatic Lesions by Eribulin Monotherapy Is Associated with Better Prognosis in Patients with Metastatic Breast Cancer. J Nippon Med Sch. 2022 Nov 9;89(5):494-499. doi: 10.1272/jnms.JNMS.2022_89-508. Epub 2022 May 30. PMID: 35644551. 3: Phillips E, Jones RL, Huang P, Digklia A. Efficacy of Eribulin in Soft Tissue Sarcomas. Front Pharmacol. 2022 Mar 30;13:869754. doi: 10.3389/fphar.2022.869754. PMID: 35444542; PMCID: PMC9014307. 4: Seshadri P, Deb B, Kumar P. Multifarious targets beyond microtubules-role of eribulin in cancer therapy. Front Biosci (Schol Ed). 2021 Dec 3;13(2):157-172. doi: 10.52586/S559. PMID: 34879468. 5: Tarasiuk O, Cavaletti G, Meregalli C. Clinical and preclinical features of eribulin-related peripheral neuropathy. Exp Neurol. 2022 Feb;348:113925. doi: 10.1016/j.expneurol.2021.113925. Epub 2021 Nov 18. PMID: 34801586. 6: Tanni KA, Truong CB, Johnson BS, Qian J. Comparative effectiveness and safety of eribulin in advanced or metastatic breast cancer: a systematic review and meta-analysis. Crit Rev Oncol Hematol. 2021 Jul;163:103375. doi: 10.1016/j.critrevonc.2021.103375. Epub 2021 Jun 2. PMID: 34087344. 7: Yuan P, Xu B. Clinical Utility of Eribulin Mesylate in the Treatment of Breast Cancer: A Chinese Perspective. Breast Cancer (Dove Med Press). 2021 Feb 24;13:135-150. doi: 10.2147/BCTT.S231298. PMID: 33658845; PMCID: PMC7917473. 8: Pedersini R, di Mauro P, Amoroso V, Parati MC, Turla A, Ghilardi M, Vassalli L, Ardine M, Volta AD, Monteverdi S, Borgonovo K, Ghidini A, Cabiddu M, Simoncini EL, Petrelli F, Berruti A, Barni S. Efficacy of Eribulin mesylate in older patients with breast cancer: A pooled analysis of clinical trial and real- world data. J Geriatr Oncol. 2020 Jul;11(6):976-981. doi: 10.1016/j.jgo.2020.03.021. Epub 2020 Apr 13. PMID: 32299685. 9: Grignani G, D'Ambrosio L. Eribulin-based treatment in patients affected by sarcomas: a case series. Future Oncol. 2020 Jan;16(1s):1-3. doi: 10.2217/fon-2019-0601. Epub 2019 Dec 16. PMID: 31840540. 10: Pizzuti L, Krasniqi E, Barchiesi G, Mazzotta M, Barba M, Amodio A, Massimiani G, Pelle F, Kayal R, Vizza E, Grassadonia A, Tomao S, Venuti A, Gamucci T, Marchetti P, Natoli C, Sanguineti G, Ciliberto G, Vici P. Eribulin in Triple Negative Metastatic Breast Cancer: Critic Interpretation of Current Evidence and Projection for Future Scenarios. J Cancer. 2019 Oct 12;10(24):5903-5914. doi: 10.7150/jca.35109. PMID: 31762800; PMCID: PMC6856581. 11: Islam B, Lustberg M, Staff NP, Kolb N, Alberti P, Argyriou AA. Vinca alkaloids, thalidomide and eribulin-induced peripheral neurotoxicity: From pathogenesis to treatment. J Peripher Nerv Syst. 2019 Oct;24 Suppl 2:S63-S73. doi: 10.1111/jns.12334. PMID: 31647152. 12: Perez-Garcia JM, Cortes J. The safety of eribulin for the treatment of metastatic breast cancer. Expert Opin Drug Saf. 2019 May;18(5):347-355. doi: 10.1080/14740338.2019.1608946. Epub 2019 May 20. PMID: 31107111. 13: O'Shaughnessy J, Kaklamani V, Kalinsky K. Perspectives on the mechanism of action and clinical application of eribulin for metastatic breast cancer. Future Oncol. 2019 May;15(14):1641-1653. doi: 10.2217/fon-2018-0936. Epub 2019 Mar 20. PMID: 30892083. 14: Fleeman N, Bagust A, Duarte R, Richardson M, Nevitt S, Boland A, Kotas E, McEntee J, Thorp N. Eribulin for Treating Locally Advanced or Metastatic Breast Cancer After One Chemotherapy Regimen: An Evidence Review Group Perspective of a NICE Single Technology Appraisal. Pharmacoecon Open. 2019 Sep;3(3):293-302. doi: 10.1007/s41669-018-0114-z. PMID: 30742256; PMCID: PMC6710448. 15: Cortes J, Schöffski P, Littlefield BA. Multiple modes of action of eribulin mesylate: Emerging data and clinical implications. Cancer Treat Rev. 2018 Nov;70:190-198. doi: 10.1016/j.ctrv.2018.08.008. Epub 2018 Aug 21. PMID: 30243063. 16: Zhao B, Zhao H, Zhao J. Incidence and clinical parameters associated with eribulin mesylate-induced peripheral neuropathy. Crit Rev Oncol Hematol. 2018 Aug;128:110-117. doi: 10.1016/j.critrevonc.2018.06.003. Epub 2018 Jun 12. Erratum in: Crit Rev Oncol Hematol. 2019 Mar;135:20. PMID: 29958626. 17: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Eribulin. 2018 Feb 20. PMID: 31643639. 18: Koliou P, Karavasilis V, Theochari M, Pollack SM, Jones RL, Thway K. Advances in the treatment of soft tissue sarcoma: focus on eribulin. Cancer Manag Res. 2018 Feb 1;10:207-216. doi: 10.2147/CMAR.S143019. PMID: 29440930; PMCID: PMC5798537. 19: Seetharam M, Kolla KR, Chawla SP. Eribulin therapy for the treatment of patients with advanced soft tissue sarcoma. Future Oncol. 2018 Jul;14(16):1531-1545. doi: 10.2217/fon-2017-0461. Epub 2018 Feb 7. PMID: 29411654. 20: Garrone O, Miraglio E, Vandone AM, Vanella P, Lingua D, Merlano MC. Eribulin in advanced breast cancer: safety, efficacy and new perspectives. Future Oncol. 2017 Dec;13(30):2759-2769. doi: 10.2217/fon-2017-0283. Epub 2017 Sep 13. PMID: 29219017.